[CH:1]1([CH3:12])[CH2:6][CH2:5][CH:4]([C:7]([OH:10])([CH3:9])[CH3:8])[CH:3]([OH:11])[CH2:2]1.N1C=CC=CC=1.[C:19](Cl)(=[O:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl>[C:19]([OH:37])(=[O:10])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[CH:1]1([CH3:12])[CH2:6][CH2:5][CH:4]([C:7]([OH:10])([CH3:9])[CH3:8])[CH:3]([OH:11])[CH2:2]1A 250 mL one necked bottomed flask, was charged with 7.0 g (0.040 moles) of 3,8-p-menthanediol, 100 mL of anhydrous methylene chloride and 6.9 g (0.87 moles) of anhydrous pyridine. 25.5 g (0.085 moles) of Linoleoyl chloride was pre-dissolved in 25-30 mL of anhydrous methylene chloride and charged into the additional funnel. The acid chloride solution was then added dropwise to the solution at room temperature under a nitrogen blanket over a period of 30 minutes. Upon completion of the addition, the reaction was stirred for two hours before the addition funnel was replaced with a reflux condenser. The reaction was then heated to reflux for two additional hours before cooling to ambient temperature and stirring overnight.
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